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When I joined the company formerly known as YouSendIt as CMO in
2012, we had a major marketing challenge in front of us: stay
with a name that the company had already outgrown or re-name and
cast aside nine years of brand equity. We chose the latter.

A year after we took the leap and became Hightail, it’s interesting to look back
and see what lessons I can pass on to other businesses -- not
only those thinking about a rebrand but startups looking for a
good name.

Too often entrepreneurs -- especially in tech -- treat a name as
an afterthought, absent-mindedly settling on either a descriptive
mouthful, something whimsical or just using a product name rather
than an actual brand name.

Having lived through the unavoidable pain of a rebrand, I know
how important it is to get your name right. So, here are seven
tips for naming (or, if necessary, re-naming) your
business.

1. Start with your brand promise. It’s vital to
know what your brand stands for before you pick your name. Your
brand promise is not what your product or service does,
it’s the deeper emotional connection it should have with your
users. It’s the way your brand should make your customers
feel.

Airbnb’s recent re-brand showed the company really understood
their brand promise with their audience. The central concept of
“belong” gets to the company’s true emotional appeal. Airbnb is
not just about cheap accommodation but about staying in places
that feel more like home with people who will become your
friends. They didn’t change their name but their entire re-brand
speaks to this idea, this brand promise.

2. Be evocative, not descriptive. Descriptive
names like YouSendIt are fine, especially when you’re first
starting out. While a descriptive name can help your product get
discovered in search marketing, ultimately, such a name will
probably limit your business. If you have taking-over-the
world-sized ambitions, follow the Apple model. In a world of
International Business Machines and Microsoft, Apple’s more
abstract name allowed them to move from computers to music
players and phones without consumers balking. It has brand
extensibility. But Apple is not just a random name plucked from
the dictionary. It evokes important symbols of human development.
It’s the fruit of the tree of knowledge in the Bible and the
object that fell on Isaac Newton’s head, inspiring the theory of
gravity. And it had personal significance for Steve Jobs
from his days living on an apple orchard commune.

3. Use a real word. It will be tempting, when
faced with the difficulty of securing URLs and trademarks, to
make your life easy by making up or misspelling a word. My advice
is don’t do it. You’re just making things harder for your
potential customers to pronounce it, spell it and remember it.

In general, people prefer the familiar. By taking familiar words
and applying them in unconventional ways, a name will stand out.

4. Consider the context. Company names are like
baby names. When it’s still in the womb, tell people a name
you’re considering and they may have a visceral reaction based on
their own experience: “I had a horrible boss named Jeremy.” But
add context in the form of a tiny, adorable human being: “Oh, he
really looks like a Jeremy.”

It’s the same with your company name. Even when you’re at the
stage of presenting options to the other decision makers, don’t
just show naked words. Put the name in context. Design a
logo (it doesn't have to be the one you actually use), mock it up
on a web page or business letterhead. Seeing the name in action
makes it easier to envision. Square is a great example. On its
own, the word hardly suggests forward thinking. But in the
context of a beautiful, square-shaped gadget that has changed how
small businesses accept payment, it’s perfect.

5. It’s not a democracy. Choosing a name is not
a democratic process. With no hard rules for success, names will
always be subjective. Getting a consensus will be difficult, so
keep your creative and approval teams as small as possible. But
once you’ve picked your name, get everyone on board.

We knew that changing our company name was controversial
internally so we made sure employees were the first to find out.
We had a grand unveiling at an all-company party with custom-made
Hightail cocktails and gave away Hightail-branded free swag. This
was partly another great way of putting the new name and logo
into context but also a subtle reminder that this was a done
deal.

6. Have a thick skin. People will hate the name
you choose -- from the baffled board member to the sneering
Internet troll. There will always be a loud minority of haters.
You just have to accept their right to criticize. Plus, you can
always be amused by the inevitable charge of obscenity.

It wasn’t long before people started comparing Airbnb’s new logo
to body parts. People told us that Hightail sounded like a
high-class escort agency or a service for “hookers on dope.” (I’m
not making that up.) For me, this reaction is like a Rorschach
personality test and says more about the accuser than your
business.

7. Don’t rebrand unless you have to. If you’re
choosing your first name, this is one last warning to get it
right the first time. If you’re thinking of re-naming your
business, think hard. Re-naming is a messy, expensive process.
Some of your customers will hate it, which is understandable
because name changes are for the company’s benefit, not the
customer’s. Even if you’re just thinking about changing your
logo, really challenge yourself to prove that it’s necessary.